I have a server that has a block rule for all RED network access and should only be able to connect through the proxy. Before configuring the proxy settings on the server I wanted to test the transparent proxy.
wget http://httpforever.com/
This runs into a timeout. I ensured that the proxy actually works:
Are there any correspondent firewall hits logged at the time you tried the first (direct) request?
On a general note, please keep in mind that the transparent proxy does not work for HTTPS requests (since transparent interception is precisely what HTTPS/TLS was designed to protect us from ), so I guess it makes more sense to turn the transparent functionality off, and go for the vanilla proxy mode. Eventually, you will need it anyways.